Synthetic Route to Chiral Tetrahydroquinoxalines via Ring-Opening of Activated Aziridines

Manas K. Ghorai*, Ashis K. Sahoo and Sarvesh Kumar

*Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India, Email: mkghoraiiitk.ac.in

M. K. Ghorai, A. K. Sahoo, S. Kumar, Org. Lett., 2011, 13, 5972-5975.

DOI: 10.1021/ol2023906

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Abstract

S_N2-type ring-opening of activated aziridines with 2-bromoanilines followed by a Pd-catalyzed intramolecular C-N bond formation enable a highly regio- and stereoselective route for the synthesis of racemic and nonracemic tetrahydroquinoxalines.

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Key Words

1,2-Diamines, Tetrahydroquinoxalines, Buchwald-Hartwig Coupling

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ID: J54-Y2011-3290